2-amino-4-(3-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile | 81829-59-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-amino-4-(3-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
• 英文别名: 2-Amino-4-(3-bromo-phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile；2-amino-4-(3-bromophenyl)-5-oxo-4,6,7,8-tetrahydrochromene-3-carbonitrile
• CAS: 81829-59-6
• 化学式: C₁₆H₁₃BrN₂O₂
• 分子量: 345.195
• InChiKey: DVFNILOIQNVJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (3-溴苯亚甲基)丙二腈 、 1,3-环己二酮 在 吗啉 作用下， 以 乙醇 为溶剂， 以89%的产率得到2-amino-4-(3-bromophenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Sharanina, L. G.; Nesterov, V. N.; Klokol, G. V., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 6, p. 1185 - 1191

  摘要：

  DOI：

文献信息

• Efficient synthesis of 2-amino-3-cyano-4H-pyran derivatives via a non-catalytic one-pot three-component reaction
  作者：Cheng-Wei Lü、Jia-Jing Wang、Fei Li、Shi-Jun Yu、Yue An

  DOI：10.1007/s11164-017-3151-9

  日期：2018.2

  Abstract A convenient one-pot multi-component strategy was conducted successfully under catalyst-free conditions employing water and PEG-400 as the efficient and cheap promoting medium. Three types and nearly 50 2-amino-3-cyano-4H-pyran annulated derivatives were synthesized in good to excellent yields by the condensation of a series of aromatic aldehydes with malononitrile and different 1,3-dicarbonyl

  摘要 在无催化剂的条件下，使用水和PEG-400作为高效廉价的促进介质，成功地成功实施了一种方便的单锅多组分策略。通过一系列芳香醛与丙二腈和不同的1,3-二羰基化合物的缩合反应，合成了三种类型的近50种2-氨基-3-氰基-4H-吡喃环化的衍生物，收率良好。宽的底物范围，系统的表征，消除的催化剂，简短的反应时间和简单的纯化程序是该方法的最佳优点。 图形概要
• Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b] pyran derivatives
  作者：Vijaya Bhaskar、Reshma Chowdary、Sheshagiri R. Dixit、Shrinivas D. Joshi

  DOI：10.1016/j.bioorg.2018.11.023

  日期：2019.3

  documented as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the for β-secretase (BACE-1) inhibitory activity of new series of tetrahydrobenzo [b] pyran derivatives. One-pot synthesis of tetrahydrobenzo [b] pyrans was carried out by condensing aromatic aldehyde, malononitrile and 1,3-cyclohexanedione using ionic liquid 1-butyl-3-methyl

  β-分泌酶（BACE1）已被广泛证明是治疗阿尔茨海默氏病的可能治疗靶标之一。在本文中，我们报告了新系列的四氢苯并[b]吡喃衍生物的合成及其对β-分泌酶（BACE-1）的抑制活性。一锅法合成四氢苯并[b]吡喃是通过在水性醇介质中使用离子液体1-丁基-3-甲基咪唑鎓氯化物（[bmIm] Cl-）缩合芳族醛，丙二腈和1,3-环己二酮来进行的。乙醇和水的比例为1：2，可使所有反应物保持在溶液中，这有助于反应并非常容易地形成产物。对合成的化合物进行BACE1抑制分析，六个化合物4d，4e，4f，4h，4i和4p在微摩尔水平显示出显着的IC50值。在这六种活性化合物中，4e是一种潜在的抑制剂，其IC50值在纳摩尔范围内。所有合成的化合物都停靠在β-分泌酶的活性位点上。
• The Implication of Electrocatalysis in MCR Strategy: Electrocatalytic Multicomponent Transformation of Cyclic 1,3-Diketones, Aldehydes and Malononitrile into Substituted 5,6,7,8-Tetrahydro-4H-Chromenes
  作者：Michail N. Elinson、Alexander S. Dorofeev、Sergey K. Feducovich、Sergey V. Gorbunov、Ruslan F. Nasybullin、Fedor M. Miloserdov、Gennady I. Nikishin

  DOI：10.1002/ejoc.200600544

  日期：2006.10

  electrochemically induced catalytic multicomponent transformation of cyclic 1,3-diketones, aldehydes and malononitrile in alcoholic solvents results in the formation of substituted 5,6,7,8-tetrahydro-4H-chromenes in 85–95 % yields. The reaction is performed in an undivided cell in the presence of sodium bromide as an electrolyte. The application of this efficient electrocatalytic method to the formation of

  环 1,3-二酮、醛和丙二腈在醇溶剂中的电化学诱导催化多组分转化导致取代 5,6,7,8-四氢-4H-色烯的形成，产率为 85-95%。在溴化钠作为电解质的存在下，该反应在未分隔的电池中进行。这种有效的电催化方法在四氢-4H-色烯的形成中的应用有利于面向多样性的大规模过程。电催化多组分反应的新概念在生态上也是合理的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• 10.3184/030823410x12891568367823
  作者：Patra, Amarendra、Mahapatra, Tanusri

  DOI：10.3184/030823410x12891568367823

  日期：——
• Synthesis of biscoumarin and dihydropyran derivatives with promising antitumor and antibacterial activities
  作者：Jing Li、Yun-Peng Sui、Jia-Jia Xin、Xin-Liang Du、Jiang-Tao Li、Hai-Ru Huo、Hai Ma、Wei-Hao Wang、Hai-Yu Zhou、Hong-Dan Zhan、Zhu-Ju Wang、Chun Li、Feng Sui、Xia Li

  DOI：10.1016/j.bmcl.2015.10.063

  日期：2015.12

  Two series of biscoumarin (1-3) and dihydropyran (4-12) derivatives were successfully synthesized as new antitumor and antibacterial agents. The molecular structures of four representative compounds 2, 4, 7 and 10 were confirmed by single crystal X-ray diffraction study. The synthesized compounds (1-12) were evaluated for their antitumor activities against human intestinal epithelial adenocarcinoma cell line (HuTu80), mammary adenocarcinoma cell line (4T1) and pancreatic cancer cell line (PANC1) and antibacterial activities against one drug-sensitive Staphylococcus aureus (S. aureus ATCC 29213) strain and three MRSA strains (MRSA XJ 75302, Mu50, USA 300 LAC). The further mechanism study demonstrated that the most potent compound 1 could obviously inhibit the proliferation of cancer cells via the mechanism to induce apoptosis. (C) 2015 Elsevier Ltd. All rights reserved.